JPH02237961A - Pentafluorobenzoic acid esters - Google Patents

Pentafluorobenzoic acid esters

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Publication number
JPH02237961A
JPH02237961A JP5777389A JP5777389A JPH02237961A JP H02237961 A JPH02237961 A JP H02237961A JP 5777389 A JP5777389 A JP 5777389A JP 5777389 A JP5777389 A JP 5777389A JP H02237961 A JPH02237961 A JP H02237961A
Authority
JP
Japan
Prior art keywords
pentafluorobenzoic acid
acid esters
formula
pentafluorobenzoic
nmr
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP5777389A
Other languages
Japanese (ja)
Inventor
Hitoshi Takeshita
竹下 齊
Akira Mori
章 森
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Shokubai Co Ltd
Original Assignee
Nippon Shokubai Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Shokubai Co Ltd filed Critical Nippon Shokubai Co Ltd
Priority to JP5777389A priority Critical patent/JPH02237961A/en
Publication of JPH02237961A publication Critical patent/JPH02237961A/en
Pending legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

NEW MATERIAL:The compound of formula (R is 8-16C alkyl). EXAMPLE:Pentafluorobenzoic acid dodecyl ester. PREPARATION:A raw material for liquid crystal display material. It exhibits liquid crystal nature in a temperature region lower than that of conventional benzoic acid esters free from fluorine. PREPARATION:The compound of formula can be produced by heating pentafluorobenzoic acid and a long-chain aliphatic alcohol in an organic solvent (e.g. benzene) using sulfuric acid as a catalyst.

Description

【発明の詳細な説明】 く産業上の利用分野〉 本発明は、下記一般式(I)で示される新規なペンタフ
ルオロ安息香酸エステル類に関するものである. (ただし式中、Rは炭素数8〜l6のアルキル基を表わ
す.) 本発明における上記一般式(I)で示される新規な化合
物ペンタフルオロ安息香酸エステル類は、フッ素を含有
していない通常の安息香酸エステル類より更に顕著な特
徴を有するもので、例えば通常のものより低温域で液晶
性を示す表示材料の原料等として有用である. 〈従来の技術〉 本発明が提供するペンタフルオロ安息香酸エステル類は
、今まで全く報告されていない.く発明の概要〉 本発明者らは、前記式(I)で示される新規なペンタフ
ルオロ安息香酸エステル類を得る製造方法を検討した.
その結果、ペンタフルオロ安息香酸と長饋の脂肪族アル
コールを硫酸を触媒にして有機溶媒中で加熱することに
よってペンタフルオロ安息香酸エステル類が得られるこ
とを見い出した. FF (ただし式中、Rは炭素数8〜l6のアルキル基を表わ
す.)で表わされる新規なペンタフルオロ安息香酸エス
テル類を提供する。
DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to novel pentafluorobenzoic acid esters represented by the following general formula (I). (However, in the formula, R represents an alkyl group having 8 to 16 carbon atoms.) The novel pentafluorobenzoic acid ester compound represented by the above general formula (I) in the present invention is a conventional compound containing no fluorine. It has more remarkable characteristics than benzoic acid esters, and is useful, for example, as a raw material for display materials that exhibit liquid crystallinity at lower temperatures than normal ones. <Prior Art> The pentafluorobenzoic acid esters provided by the present invention have not been reported at all to date. Summary of the Invention The present inventors investigated a method for producing a novel pentafluorobenzoic acid ester represented by the above formula (I).
As a result, we discovered that pentafluorobenzoic acid esters can be obtained by heating pentafluorobenzoic acid and a long-term aliphatic alcohol in an organic solvent using sulfuric acid as a catalyst. A novel pentafluorobenzoic acid ester represented by FF (wherein R represents an alkyl group having 8 to 16 carbon atoms) is provided.

なお本発明にかかるペンタフルオロ安息香酸エステル類
の製造方法は、上記のものに限定されないことはもちろ
んである。
It goes without saying that the method for producing pentafluorobenzoic acid esters according to the present invention is not limited to the above method.

以下、本発明を実施例により更に具体的に説明し、得ら
れたこれらの新規物質を特定するための分析結果をも同
時に示す。
Hereinafter, the present invention will be explained in more detail with reference to Examples, and the analysis results for identifying these new substances obtained will also be shown at the same time.

災施炎上 無水ベンゼン(I 0mffi)にペンタフルオロ安息
香酸(500■,  2.3 6ms+ol) 、n−
ドデシルアノレコーノレ(Z I g.  1 1.0
mmol)および硫酸(触媒量)を加え、モレキエラー
シーブ3Aで水を除去しながら、窒素気流下、11時間
加熱還流した.反応後溶媒を除去し、酢酸エチル(20
ml)を加え、水洗後硫酸マグネシウムで乾燥し、?圧
下溶媒を留去した.残渣をシリカゲルカラムクロマトグ
ラフィ−(酢酸エチルで流出)で分離精製し、ペンタフ
ルオロ安息香酸ドデシルエステルを収率86%で得た。
Anhydrous benzene (I0mffi) was mixed with pentafluorobenzoic acid (500μ, 2.36ms+ol), n-
Dodecyl anoleconole (Z I g. 1 1.0
mmol) and sulfuric acid (catalytic amount) were added, and the mixture was heated under reflux for 11 hours under a nitrogen stream while removing water using a Molecule sieve 3A. After the reaction, the solvent was removed and ethyl acetate (20
ml), washed with water and dried with magnesium sulfate. The solvent was distilled off under pressure. The residue was separated and purified by silica gel column chromatography (elution with ethyl acetate) to obtain pentafluorobenzoic acid dodecyl ester in a yield of 86%.

無色液体 ’H−NMR  (CDCl3) 60.88(3H.t,J−7.1Hz), 1.2−
1.5(I8H,m).1.75(2H,quint,
J=7.1Hz). 4.38(2H.t,J=6.6
11z)”C−NMR (CDC11) δ14.1. 22.8. 25.8, 28.5, 
29.2, 29.4, 29.5,29.6, 29
.7. 32.0, 67.1, 108.5,130
.0(Jcy■250.4HZ),143.1(JCF
=259.2}+2),145.2(Jcy■252.
4Hz). 159.2” F−NMR (CDC l
 .+)δ1.3, 12,7. 23.4 (2:1
:2)MS  m/z  380(M”),  38N
N”+1).  382(M”+2)実施例2〜5 実施例tにおいてn−ドデシルアルコールの代りに、下
記表1のアルコールを用いた以外実施例1と同様に操作
してそれぞれのエステルを得た.?下に各実施例で得ら
れた化合物の物性値を示す. 実隻貫主皇囮査1 無色液体 ’H−NMR  (CDCj! !) δ0.88(3H,t,J=7.0Hz), 1.2−
1.5(I0H.+++),1.76(2H.quin
t,J=7.0Hz), 4.38(2H,tj=6.
611z)I3C−Nl’lR (CD(f!:+)δ
14.1, 22.7, 25.8. 28.5. 2
9.2. 29.8, 31.8,67.1, 108
.7, 137.9(Jc,=244.5Hz),14
3.2(Jcy■254.3Hz), 145.5(J
cr−264.1Hz).159.2 I叩一NMR (CDC It 3) δ1.3. 12.7. 23.4 (2:1:2)M
S  s/z  324(M”),  325(M”+
1),  326(M”+2)夫施桝l夏止介批 無色液体 ’H−NMR  (CDC 1 3) 60.88(3H,t,J=7.1Hz). 1.3−
1.5(I4H,m),1.77(2H,quint,
J−7.1Hz), 4.38(211,t,J=6.
611z)? ”C−NMR  (CDC l a)δ
 14.1. 22.9. 26.1. 2B.7, 
29.5. 29.(i. 29.81.29.84,
  32.2,  67.1,  108.9,138
.0(Jcr=250.4Hz) ,  143.4(
Jcr=259.2tlz) ,145.6(Jcr■
253.3Hz),159.119F−NMI?  (
CDCA■) δ 1.3,  12.7,  23.4  (2:1
:2)MS m/z 352(Mつ, 353(M”+
1), 354(M”+2)HMS Calcd  for  C.d{2,OzFs  :
  352.1460Found          
    :  352.1454!施炭土互化金璽 無色液体 ’II−NMR  (CDC l 3)δ0.88(3
8,t,J=7.0Hz). 1.3−1.5(22H
,m).1.75(2H,quint.J=7.0Hz
), 4.38(28,t,J−6.6Hz)l3C−
NMR (CDCfz) δ14.4, 23.0, 26.0. 2B.7, 
29.4, 29.7. 29.76,29.84. 
29.9, 30.0, 32.2, 67.3, 1
08.9,137.9(Jey=250.4Hz). 
143.4(Jcp・259.2Hz).?45.6(
Jcr=252.4Hz),159.4’ ”P−NM
R  (CDC j! 3)δ 1.3.  12.7
.  23.4  (2:l:2)MS m/z 40
8(M”).  409(M”+1).  410(M
”+2)HMS Calcd  for  CtrHz*OtFs  :
  40B.2086Found          
    :  40B.2058ス[日バし1責 無色液体 ’H−NMR  (CDCj! !) δ0,88(3}1,t,J=7.3Hz). 1.3
−1.5(26H,a+),1.76(2B,qutn
t.J−7.311z). 4.38(2[1.t,J
=6.6Hz)” C−NMR (CDC l 3) δ14.3. 23,0, 26.1. 2B.7. 
29.4. 29.7. 29.8,29.85, 2
9.94, 29.99. 30.02, 32.2,
 67.3,108.9, 138.0(Jar−25
6.311z) .143.4(Jcr=259.2H
z), 145.7(Jcr■264.1Hz).15
9.4
Colorless liquid 'H-NMR (CDCl3) 60.88 (3H.t, J-7.1Hz), 1.2-
1.5 (I8H, m). 1.75 (2H, quint,
J=7.1Hz). 4.38 (2H.t, J=6.6
11z)"C-NMR (CDC11) δ14.1. 22.8. 25.8, 28.5,
29.2, 29.4, 29.5, 29.6, 29
.. 7. 32.0, 67.1, 108.5, 130
.. 0 (Jcy■250.4HZ), 143.1 (JCF
=259.2}+2), 145.2(Jcy■252.
4Hz). 159.2” F-NMR (CDCl
.. +) δ1.3, 12, 7. 23.4 (2:1
:2) MS m/z 380(M”), 38N
N"+1). 382 (M"+2) Examples 2 to 5 Each ester was prepared in the same manner as in Example 1 except that in Example t, the alcohol shown in Table 1 below was used instead of n-dodecyl alcohol. Obtained. ? The physical property values of the compounds obtained in each example are shown below. Real Ship Kanshu Emperor Decoy Inspection 1 Colorless Liquid 'H-NMR (CDCj!!) δ0.88 (3H, t, J=7.0Hz), 1.2-
1.5 (I0H.+++), 1.76 (2H.quin
t, J=7.0Hz), 4.38 (2H, tj=6.
611z) I3C-Nl'lR (CD(f!:+)δ
14.1, 22.7, 25.8. 28.5. 2
9.2. 29.8, 31.8, 67.1, 108
.. 7, 137.9 (Jc, = 244.5Hz), 14
3.2 (Jcy■254.3Hz), 145.5 (J
cr-264.1Hz). 159.2 I Hit NMR (CDC It 3) δ1.3. 12.7. 23.4 (2:1:2)M
S s/z 324 (M”), 325 (M”+
1), 326 (M”+2) Colorless liquid H-NMR (CDC 1 3) 60.88 (3H, t, J=7.1Hz). 1.3-
1.5 (I4H, m), 1.77 (2H, quint,
J-7.1Hz), 4.38 (211,t, J=6.
611z)? "C-NMR (CDCl a) δ
14.1. 22.9. 26.1. 2B. 7,
29.5. 29. (i. 29.81.29.84,
32.2, 67.1, 108.9, 138
.. 0(Jcr=250.4Hz), 143.4(
Jcr=259.2tlz) ,145.6(Jcr■
253.3Hz), 159.119F-NMI? (
CDCA ■) δ 1.3, 12.7, 23.4 (2:1
:2) MS m/z 352 (M two, 353 (M"+
1), 354 (M”+2) HMS Calcd for C.d{2, OzFs:
352.1460Found
: 352.1454! Colorless liquid 'II-NMR (CDC l 3) δ0.88 (3
8,t,J=7.0Hz). 1.3-1.5 (22H
, m). 1.75 (2H, quint.J=7.0Hz
), 4.38 (28, t, J-6.6Hz) l3C-
NMR (CDCfz) δ14.4, 23.0, 26.0. 2B. 7,
29.4, 29.7. 29.76, 29.84.
29.9, 30.0, 32.2, 67.3, 1
08.9, 137.9 (Jey=250.4Hz).
143.4 (Jcp・259.2Hz). ? 45.6(
Jcr=252.4Hz), 159.4' ”P-NM
R (CDC j! 3) δ 1.3. 12.7
.. 23.4 (2:l:2)MS m/z 40
8 (M”). 409 (M”+1). 410 (M
”+2) HMS Calcd for CtrHz*OtFs:
40B. 2086Found
: 40B. 2058S [Sunba 1 Responsibility Colorless Liquid'H-NMR (CDCj!!) δ0,88(3}1,t,J=7.3Hz). 1.3
-1.5 (26H, a+), 1.76 (2B, qutn
t. J-7.311z). 4.38 (2[1.t, J
=6.6Hz)" C-NMR (CDCl3) δ14.3.23.0, 26.1.2B.7.
29.4. 29.7. 29.8, 29.85, 2
9.94, 29.99. 30.02, 32.2,
67.3, 108.9, 138.0 (Jar-25
6.311z). 143.4 (Jcr=259.2H
z), 145.7 (Jcr■264.1Hz). 15
9.4

Claims (1)

【特許請求の範囲】 1、下記一般式( I )で示されるペンタフルオロ安息
香酸エステル類。 ▲数式、化学式、表等があります▼( I ) (ただし式中、Rは炭素数8〜16のアルキル基を表わ
す。)
[Claims] 1. Pentafluorobenzoic acid esters represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (However, in the formula, R represents an alkyl group having 8 to 16 carbon atoms.)
JP5777389A 1989-03-13 1989-03-13 Pentafluorobenzoic acid esters Pending JPH02237961A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP5777389A JPH02237961A (en) 1989-03-13 1989-03-13 Pentafluorobenzoic acid esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP5777389A JPH02237961A (en) 1989-03-13 1989-03-13 Pentafluorobenzoic acid esters

Publications (1)

Publication Number Publication Date
JPH02237961A true JPH02237961A (en) 1990-09-20

Family

ID=13065188

Family Applications (1)

Application Number Title Priority Date Filing Date
JP5777389A Pending JPH02237961A (en) 1989-03-13 1989-03-13 Pentafluorobenzoic acid esters

Country Status (1)

Country Link
JP (1) JPH02237961A (en)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J CHROMATOGRAPHY=1985 *

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